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SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!

Photo gallery for SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!

Welcome home!
Lush surroundings
Private front porch
Enjoy vibrant surroundings
Open floor plan with powder room

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4106.1 sq m

Popular amenities

  • Private pool
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Key West, FL
  • Place, Key West Naval Station
    ‪4 min walk‬
  • Place, Duval Street
    ‪15 min walk‬
  • Place, Southernmost Point
    ‪17 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 Double Murphy Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Dining area

About this property

SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!

CATCH YOUR SECOND WIND…
Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambiance. Equipped with 2 bedrooms and 2 bathrooms, this home welcomes you into a peaceful setting within the desirable district of The Meadows.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS & AMENITIES…
Welcome in to an inviting, open floor plan boasting vaulted ceilings, hardwood floors and stunning wooden beams ready to entertain your crew for your getaway to Paradise. A fully equipped kitchen allows for seamless meal prep to enjoy together at the dining table for 6. Enjoy the bright and cheery living space with cozy furnishings and a TV for your lazy days in with gorgeous views beyond pocket doors of your outdoor oasis. This home is equipped with Youtube TV for live steaming.

SLEEPING ARRANGEMENTS…
Sleep tight in one of two cozy bedrooms both equipped with storage space and flat screen TVs. The primary king suite comes with an en suite bathroom with a double sink vanity and jet tub/shower combination. The second bedroom has a Queen Murphy bed and desk so the room can also be used as an office space. The second bathroom lies in the hallway with a shower/tub combination.

OUTDOOR LIVING…
Soak up your surroundings as you head out to your private backyard dream tucked within lush and vibrant foliage. Cool off in the pool which comes heated in the winter month and dine al fresco in the island breeze equipped with a gas grill. Lounge on your private front porch over your morning cup of coffee as you dream of your days adventures ahead. The Meadows district is a charming and convenient location to downtown Key West, yet tucked away for a peaceful evenings rest.

PARKING...
There is one parking space making coming and going a breeze.

PETS...
Dogs are considered at this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests.

MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
Pool/hot tub heating fee (if applicable)
Pet fee (if applicable)

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last).  We may consider alternate dates if the calendar allows or if the owner will make an exception.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

CANCELLATION...
Bookings canceled at least 90 days before the start of stay will receive a 100% refund.

Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).

YOUR SLICE OF PARADISE AWAITS…

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number 25230-138749

About the area

Key West

Located by the sea, this holiday home is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Map
Key West, FL

What's nearby

  • Key West Naval Station - 4 min walk - 0.4 km
  • Duval Street - 15 min walk - 1.3 km
  • Clarence S. Higgs Memorial Beach Park - 15 min walk - 1.3 km
  • South Beach - 16 min walk - 1.3 km
  • Southernmost Point - 17 min walk - 1.5 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 7 min drive

Restaurants

  • ‪Dions Truman & White - ‬3 min walk
  • ‪Circle K - ‬9 min walk
  • ‪Sandy's Café - ‬6 min walk
  • ‪The Dive Bar Shirt Club - Grub House - ‬15 min walk
  • ‪Moose Lodge - ‬6 min walk

Frequently asked questions

Does SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?

As of 11 April 2026, prices found for a 1-night stay for 2 adults at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! on 1 June 2026 start from NZ$459, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?

On-site parking is available at the property.

What time is check-in at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?

Check-in begins at 4:00 PM.

What time is check-out at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?

Checkout is at 10:00 AM.

Where is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! located?

Located in Key West Historic District, this holiday home is within a 15-minute walk of The Unitarian Universalist Fellowship of Key West and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 1 mile (2 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

6.0/10

Cleanliness

10/10

Check-in

6.0/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

A guest from Montreal, Quebec

Best vacation!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Brian was helpfull I loved my stay and I even rebooked for next year
Response from VrboOwner on 18 February 2023
Thank you for your wonderful review Merci! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next year. Thank you for being our guest!
From a partner site

10/10 Excellent

Anonymous

Great experience

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I spent two months at this property and loved it. It is a peaceful neighborhood, and the property is beautiful—just as advertised in the pictures. I recommend it highly. Also, the property manager and management company are first rate and very responsive.
Response from VrboOwner on 9 May 2025
Thank you so much for your kind words Peirce! We're thrilled to hear you had such a great experience during your two-month stay. It’s wonderful to know the home and neighborhood met your expectations and that our team could make your time here even more enjoyable. We truly appreciate your recommendation and hope to welcome you back anytime you're in Key West!
From a partner site

10/10 Excellent

John R.

Perfect house for the summer

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We rented this house for 3 months, and was close enough to all the action, and also super convenient for parking and access to the park to walk our dogs twice a day. We loved it. Not to mention a pool to cool down in!
Response from VrboOwner on 2 September 2024
Thank you for your wonderful review John. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!
From a partner site

10/10 Excellent

Melissa S.

Wonderful trip

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Second Wind property was a wonderful respite from the cold climes of Wyoming. The location and proximity was perfect for us. The neighborhood was quiet, neighbors lovely, house was comfortable. Team Truman and Company are excellent!
Response from VrboOwner on 28 June 2022
Thank you for your incredible review Melissa! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!
From a partner site

10/10 Excellent

Page W.

March 2023 Second Wind Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful cottage in great location in Key West. Rental team superb throughout, property manager Brian was great and immediately responded to any issues or concerns. Highly recommend.
Response from VrboOwner on 8 April 2023
Thank you for sharing a review of your recent experience John. Our team here at Best of Key West Rentals is committed to providing high-quality guest service, and we’re thrilled to hear that we made a good impression on you. We hope you’ll visit us again soon.
From a partner site

10/10 Excellent

Alicia W.

Wonderful Retreat

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was exactly as we hoped it would be. Good location with off street parking (a definite plus). The one problem that we had (lock problem) was quickly and efficiently solved by Brian. Definitely would recommend to friends 🤙.
Response from VrboOwner on 16 July 2022
Thank you for this great review Vincent! We are thrilled you enjoyed the property and hope to host you again in the future!
From a partner site

10/10 Excellent

Dwight U.

Second Stay at Second Wind.

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was our second stay at this deluxe house on Albury Street. The perfect home in Key West. We brought our bikes and never drove our car again for the month. You are an easy bike ride from Duval Street and all it has to offer. Once you are home in this private little oasis the fun really begins. The back yard and pool are very secluded and very beautiful. A tropical heaven!
Response from VrboOwner on 22 March 2023
Thank you for your wonderful review Dwight. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!
From a partner site

10/10 Excellent

John M.

A pleasant stay at Second Wind

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We're having a terrific time. We've been here for 7 weeks with 10 days to go. The location is perfect for us, in a quiet neighbourhood (the Meadows) but an easy walk or bike ride to anything we want to do. The house itself is bright and airy. The housekeeping and pool/landscaping services are excellent. The property management team has been very helpful and are quick to respond. If we could make some minor suggestions, they would be: to add towel racks to the principal bathrooms and more dishware, especially saucers for the cups, in the kitchen (which is very well-appointed otherwise). The addition of a light over the dining room table would be helpful. We find the living room sofa a bit too deep to be comfortable for TV viewing. These are relatively minor issues and we've loved our stay here.
Response from VrboOwner on 20 July 2024
Thank you for your feedback on your winter stay Alan. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will rely back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!
Verified

8/10 Good

Timothy D.

Liked: Check-in, location, listing accuracy

Misses

No garbage disposal or ice maker. The freezer would stay open after you shut the fridge. The landscapers came once during our stay and they were there on the day we left. The yard and street were a mess. The lack of curtains in the living room provided NO privacy. It was like we were in a fish bowl. The light over the stove did not work. The front gate is falling apart.
Stayed 29 nights in Nov 2021
Response from VrboOwner on 11 January 2022
Dear Timothy, we are sorry you felt short of your expectations, however the home isn't advertised as having a garbage disposal or an ice maker. The landscapers come twice a month, unfortunately your stay was right in the middle of the time when the tree in the front was shedding its leaves so unless they came everyday, the grounds were never going to be free of leaves. The lush surrounding vegetation provides a lot of privacy, it is a shame you felt like a fish in a bowl., most of our guests enjoy the indoor/outdoor feel. We are addressing the other issues you mentioned and would love the get a second chance at finding you the perfect property next time you visit the island!

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

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